You’ve previously said you were “very poor” growing up as a child. What lessons did you learn from that?Andy Woodman, via TwitterI remember that time of my life, and it is true we didn’t have money to spend, but I grew up in a wonderful family – a working family. It was a quiet, peaceful time. My father never shouted at me. I lived with my whole family; my father, my mother, my sister and my grandparents. That time built my character. My family worked on the land – they were farmers. We made Parmesan cheese. I still know how to make it to this day. Every morning we would take the milk from the cows to make the cheese.

What was the highlight of your time at Milan as a player, and what was it like to play with so many legends of the game?Don Keeper, via Facebook I chose the right time to go to Milan, didn’t I? It was a really, really fantastic team, and we played for a manager who knew exactly what he wanted. Arrigo Sacchi was doing something new in football with how we were organised, and he taught us to express ourselves, which helped us to stay at the top. I had a great relationship with Paolo Maldini and Franco Baresi, but Sacchi was the key.

The most famous eyebrow in football

Which was the better team: Milan during the 1980s or the Barcelona side of 2015?Terry Menton, via Twitter[Laughs] That is a really difficult one to answer because football has changed so much since the ’80s. Honestly, I think Barcelona play with more intensity now. But it is hard to compare because the rules of the game have changed, especially with the offside rule. It is much easier to score goals these days because it is harder to keep the defensive line so high. Now, you are offside only if you are the player touching the ball or near it, whereas when I played for Milan everyone had to be behind the line.

FACT FILE

Date of birth: June 10, 1959

Place of birth: Reggiolo, Italy

Position: Midfielder

International: 1981-91 Italy 26 (1)

What did you learn from working as Arrigo Sacchi’s assistant with Italy at the 1994 World Cup? How did you console Roberto Baggio after his penalty miss in the final?Johnson Neil, via TwitterBeing with him for three years was a good experience. I learned the methodology of training, and also about strategy and focusing on the little details. I didn’t speak to Baggio after the final, because what can you really say? Our two best penalty-takers were him and Baresi, and they both missed. It is a lottery; it is a mental situation and not a technical one.

Why did the Juventus fans not like you when you managed there? Did it feel like revenge when you beat them with Milan in the 2003 Champions League Final?Nick Gove, BatterseaThe problem with me and the Juventus fans was that I had been a Milan and Roma player, and they didn’t like that. During the 1980s there was a big rivalry between Juventus and Milan – they were always going for the title – and before that in 1983 I had been part of the Roma team who had beaten Juventus to the title; a great Juventus side, too, with Platini, Boniek, Gentile, Scirea and Zoff. I wouldn’t call it revenge, but it was strange to play the final of the Champions League against a team that had sacked me not long before. But that was the first time I had ever won the Champions League as a manager, so my emotions were not of revenge – just of happiness.

The regret is that I should have won more titles with Milan because I had a fantastic squad. We did well in the Champions League, playing in three finals and winning two

You’ve won more Champions League trophies than Serie A titles: three to one. Is it a regret you didn’t win more?James Burgett, PisaYes, a little bit, because at Milan I had the possibility to win more titles but a lot of the time we finished second. I also came second with Parma in 1997. The regret is that I should have won more titles with Milan because I had a fantastic squad. We did well in the Champions League, playing in three finals and winning two, but yes, we should have won more league titles.

How do you explain losing the 2005 Champions League Final to Liverpool after leading 3-0 at half-time? Could you have done anything differently to stop their incredible comeback in Istanbul?Lance Baumatan, LondonI look back at this quite often, but I don’t think there is anything I could have done differently. It was all about six minutes. We played for 114 minutes; Liverpool played for six minutes. That’s the truth of it. It was a very strange game. You know, I took this Milan team to three Champions League finals, and 2005 was actually the best we played – but it was the only one we lost! [FFT: Were your players celebrating at half-time? Did they think they had already won?] No, no, this is bullshit. Bullshit! We were very happy because we had played a fantastic first half, but we knew we had another half to play. Even at 3-3 we should have won it in the last minute when [Andriy] Shevchenko had a chance in front of goal, but [Jerzy] Dudek saved it.

Both Gerrard and the 2005 Champions League Final proved beyond Ancelotti's reach

Your Chelsea side won the Premier League in record style in 2009-10, breaking the 100-goal barrier. What was your secret? Laurie Arbor, BrightonWe just had great players – guys like Nicolas Anelka, Didier Drogba, Frank Lampard and Michael Ballack – and a great shape that season. That was the key. Above all, the players were comfortable with their positions.

I was not happy with Ray being sacked as it was during the season. I wanted to keep him

What went wrong in your second season at Chelsea? How did you feel about Ray Wilkins leaving without you knowing?Lester Scott, via TwitterWe started well, then had a lot of injuries. We had [John] Terry, [Michael] Essien and Drogba out. I was not happy with Ray being sacked as it was during the season. I wanted to keep him.